Tag: IT Security

I’m still digging into the details of it, but in essence, the “Armadillo” (Crunchy on the outside, soft on the inside) protection model is broken (sometimes known as the “Fortress Model”). You assume that your impenetrable network boundary will prevent attackers from getting to your sensitive data. While this may stop them for a while, what you’re actually seeing here is one part of a complex protection system, however many organisations miss the fact that this is just one part.

The examples used in the onlyonline content I’ve found about this refer to a burglary.

In this context, your “Protection” (P) is measured in time. Perhaps you have hardened glass that takes 20 seconds to break.

Next, we evaluate “Detection” (D) which is also, surprisingly enough, measured in time. As the glass is hit, it triggers an alarm to a security facility. That takes 20 seconds to respond and goes to a dispatch centre, another 20 seconds for that to be answered and a police officer dispatched.

The police officer being dispatched is the “Response” (R). The police take (optimistically) 2 minutes to arrive (it was written in the 90’s so the police forces weren’t decimated then).

So, in the TBS system, we say that Detection (D) of 40 seconds plus Response (R) of 120 seconds = 160 seconds. This is greater than Protection (P) of 20 seconds, so we have an Exposure (E) time of 140 seconds E = P – (D + R). The question that is posed is, how much damage can be done in E?

So, compare this to your average pre-automation SOC. Your firewall, SIEM (Security Incident Event Management system), IDS (Intrusion Detection System) or WAF (Web Application Firewall) triggers an alarm. Someone is trying to do something (e.g. Denial Of Service attack, password spraying or port scanning for vulnerable services) a system you’re responsible for. While D might be in the tiny fractions of a minute (perhaps let’s say 1 minute, for maths sake), R is likely to be minutes or even hours, depending on the refresh rate of the ticket management system or alarm system (again, for maths sake, let’s say 60 minutes). So, D+R is now 61 minutes. How long is P really going to hold? Could it be less than 30 minutes against a determined attacker? (Let’s assume P is 30 minutes for maths sake).

Let’s do the calculation for a pre-automation SOC (Security Operations Centre). P-(D+R)=E. E here is 31 minutes. How much damage can an attacker do in 31 minutes? Could they put a backdoor into your system? Can they download sensitive data to a remote system? Could they pivot to your monitoring system, and remove the logs that said they were in there?

If you consider how much smaller the D and R numbers become with an event driven SOAR (Security Orchestration and Automation Response) system – does that improve your P and E numbers? Consider that if you can get E to 0, this could be considered to be “A Secure Environment”.

Also, consider the fact that many of the tools we implement for security reduce D and R, but if you’re not monitoring the outputs of the Detection components, then your response time grows significantly. If your Detection component is misconfigured in that it’s producing too many False Positives (for example, “The Boy Who Cried Wolf“), so you don’t see the real incident, then your Response might only be when a security service notifies you that your data, your service or your money has been exposed and lost. And that wouldn’t be good now… Time to look into automation 😁

Hello! Maybe you just got a sneeking suspicion that a website you trusted isn’t behaving right, perhaps someone told you that “unusual content” is being posted in your name somewhere, or, if you’re really lucky, you might have just had an email from a website like “HaveIBeenPwned.com” or “Firefox Monitor“. It might look something like this:

An example of an email from the service “Have I Been Pwned”

Of course, it doesn’t feel like you’re lucky! It’s OK. These things happen quite a lot of the time, and you’re not the only one in this boat!

How bad is it, Doc?

First of all, don’t panic! Get some idea of the scale of problem this is by looking at a few key things.

How recent was the breach? Give this a score between 1 (right now) and 10 (more than 1 month ago).

How many websites and services do you use this account on? Give this a score between 1 (right now) and 10 (OMG, this is *my* password, and I use it everywhere).

How many other services would use this account to authenticate to, or get a password reset from? Give this a score between 1 (nope, it’s just this website. We’re good) and 10 (It’s my email account, and everything I’ve ever signed up to uses this account as the login address… or it’s Facebook/Google and I use their authentication to login to everything else).

How much does your reputation hang on this website or any other websites that someone reusing the credentials of this account would get access to? Give this a score between 1 (meh, I post cat pictures from an anonymous username) and 10 (I’m an INFLUENCER HERE dagnamit! I get money because I said stuff here and/or my job is on that website, or I am publicly connected to my employer by virtue of that profile).

(Optional) If this is from a breach notification, does it say that it’s just email addresses (score 1), or that it includes passwords (score 5), unencrypted or plaintext passwords (score 8) or full credit card details (score 10)?

Once you’ve got an idea of scale (4 to 40 or 5 to 50, depending on whether you used that last question), you’ve got an idea of how potentially bad it is.

Take action!

Make a list of the websites you think that you need to change this password on.

Start with email accounts (GMail, Hotmail, Outlook, Yahoo, AOL and so on) – each email account that uses the same password needs to be changed, and this is because almost every website uses your email address to make a “password” change on it! (e.g. “Forgot your password, just type in your email address here, and we’ll send you a reset link“).

Next up is *this* website, the one you got the breach notification for. After all, you know this password is “wild” now!

Change some passwords

This is a bit of a bind, but I’d REALLY recommend making a fresh password for each of those sites. There are several options for doing this, but my preferred option is to use a password manager. If you’re not very tech savvy, consider using the service Lastpass. If you’re tech savvy, and understand how to keep files in sync across multiple devices, you might be interested in using KeePassXC (my personal preference) or BitWarden instead.

No really. A fresh password. Per site. Honest. And not just “MyComplexPassw0rd-Hotmail” because there are ways of spotting you’ve done something like that, and when they come to your facebook account, they’ll try “MyComplexPassw0rd-Facebook” just to see if it gets them in.

ℹ️ Using a password manager gives you a unique, per-account password. I just generated a fresh one (for a dummy website), and it was 2-K$F+j7#Zz8b$A^]qj. But, fortunately, I don’t have to remember it. I can just copy and paste it in to the form when I need to change it, or perhaps, if you have a browser add-on, that’ll fill it in for you.

Making a list, and checking it twice!

Fab, so you’ve now got a lovely list of unique passwords. A bit like Santa, it’s time to check your list again. Assume that your list of sites you just changed passwords for were all compromised, because someone knew that password… I know, it’s a scary thought! So, have a look at all those websites you just changed the password on and figure out what they have links to, then you’ll probably make your list of things you need to change a bit bigger.

Not sure what they have links to?

Well, perhaps you’re looking at an email account… have a look through the emails you’ve received in the last month, three months or year and see how many of those come from “something” unique. Perhaps you signed up to a shopping site with that email address? It’s probably worth getting a password reset for that site done.

Perhaps you’re looking at a social media site that lets you login to other services? Check through those other services and make sure that “someone” hasn’t allowed access to a website they control. After all, you did lose access to that website, and so you don’t know what it’s connected to.

Also, check all of these sites, and make sure there aren’t any unexpected “active sessions” (where someone else is logged into your account still). If you have got any, kick them out :)

OK, so the horse bolted, now close the gate!

Once you’ve sorted out all of these passwords, it’s probably worth looking at improving your security in general. To do this, we need to think about how people get access to your account. As I wrote in my “What to do when your Facebook account gets hacked?” post:

What if you accidentally gave your password to someone? Or if you went to a website that wasn’t actually the right page and put your password in there by mistake? Falling prey to this when it’s done on purpose is known as social engineering or phishing, and means that someone else has your password to get into your account.

The easiest way of locking this down is to use a “Second Factor” (sometimes abbreviated to 2FA). You need to give your password (“something you know”) to log into the website. Now you also need something separate, that isn’t in the same store. If this were a physical token (like a SoloKey, Yubikey, or a RSA SecurID token), it’d be “something you have” (after all, you need to carry around that “token” with you), but normally these days it’s something on your phone.

Some places will send you a text message, others will pop up an “approve login” screen (and, I should note, if you get one and YOU AREN’T LOGGING IN, don’t press “approve”!), or you might have a separate app (perhaps called “Google Authenticator”, “Authy” or something like “Duo Security”) that has a number that keeps changing.

You should then finish your login with a code from that app, SMS or token or reacting to that screen or perhaps even pressing a button on a thing you plug into your computer. If you want to know how to set this up, take a look at “TwoFactorAuth.org“, a website providing access to the documentation on setting up 2FA on many of the websites you currently use… but especially do this with your email accounts.

I had the privilege today to attend BSIDES Liverpool 2019. BSIDES is a infosec community conference. The majority of the talks were recorded, and I can strongly recommend making your way through the content when it becomes available.

Full disclosure: While my employer is a sponsor, I was not there to represent the company, I was just enjoying the show. A former colleague (good friend and, while he was still employed by Fujitsu, an FDE – so I think he still is one) is one of the organisers team.

The first talk I saw (aside from the welcome speech) was the keynote by Omri Segev Moyal (@gelossnake) about how to use serverless technologies (like AWS Lambda) to build a malware research platform. The key takeaway I have from that talk was how easy it is to build a simple python lambda script using Chalice. That was fantastic, and I’m looking forward to trying some things with that service!

For various reasons (mostly because I got talking to people), I missed the rest of the morning tracks except for the last talk before lunch. I heard great things about the Career Advice talk by Martin King, and the Social Engineering talk by Tom H, but will need to catch up on those on the videos released after.

Just before lunch we received a talk from “The Chief” (from the Channel 4 TV Series “Hunted”), Peter Bleksley, about an investigation he’s currently involved in. This was quite an intense session, and his history (the first 1/4 of his talk) was very interesting. Just before he went in for his talk, I got a selfie with him (which is the “Featured Image” for this post :) )

After lunch, I sat on the Rookies Track, and saw three fantastic talks, from Chrissi Robertson (@frootware) on Imposter Syndrome, Matt (@reversetor) on “Privacy in the age of Convenience” (reminding me of one of my very early talks at OggCamp/BarCamp Manchester) and Jan (@janfajfer) about detecting data leaks on mobile devices with EVPN. All three speakers were fab and nailed their content.

Next up was an unrecorded talk by Jamie (@2sec4u) about WannaCry, as he was part of the company who discovered the “Kill-Switch” domain. He gave a very detailed overview of the timeline about WannaCry, the current situation of the kill-switch, and a view on some of the data from infected-but-dormant machines which are still trying to reach the kill-switch. A very scary but well explained talk. Also, memes and rude words, but it’s clearly a subject that needed some levity, being part of a frankly rubbish set of circumstances.

After that was a talk from (two-out-of-six of) The Beer Farmers. This was a talk (mostly) about privacy and the lack of it from the social media systems of Facebook, Twitter and Google. As I listen to The Many Hats Club podcast, on which the Beer Farmers occasionally appear, it was a great experience matching faces to voices.

We finished the day on a talk by Finux (@f1nux) about Machiavelli as his writings (in the form of “The Prince”) would apply to Infosec. I was tempted to take a whole slew of photos of the slide deck, but figured I’d just wait for the video to be released, as it would, I’m sure, make more sense in context.

There was a closing talk, and then everyone retired to the bar. All in all, a great day, and I’m really glad I got the opportunity to go (thanks for your ticket Paul (@s7v7ns) – you missed out mate!)

See, one of the things I (mis-)use Ansible for is to build Azure, AWS and OpenStack environments (instead of, perhaps, using Terraform, Cloud Formations or Heat Stacks). As a result, I frequently want to set complex passwords that are unique to *that environment* but that aren’t new for each build. My way of doing this is to run a delegated task to generate files in host_vars. Here’s a version of the playbook I use for that!

---
- hosts: all
# Don't gather facts - for this test, we don't have access to any actual
# hosts. This replicates an "infrastructure build" environment where you
# might not have the hosts actually created at this point!
gather_facts: false
vars:
# This next block looks up or generates the passwords for each host.
# - ansible_password is defined as part of the inventory.
# - machine_password is the generated password, stored in host_vars.
# - PASSWORD is an environment variable, which can be specified on the
# command line.
# - project_password is a playbook-wide password, if all the machines
# need to have a common password.
# - Otherwise, generate a 12 character long password using A-Za-z0-9,
# and suffix it with _ and the common suffix (default "password").
password: |
{%- if ansible_password is defined -%}
{{ ansible_password }}
{%- elif machine_password is defined -%}
{{ machine_password }}
{%- elif lookup('env', 'PASSWORD') != '' -%}
{{ lookup('env', 'PASSWORD') }}
{%- else -%}
{{ project_password |
default(
lookup ('password', '/dev/null length=12 chars=lowercase,uppercase,digits') +
'_' +
project_password_suffix | default('Password')
)
}}
{%- endif -%}
tasks:
# Initially we need to ensure that the host_vars directory is created.
- name: Create host_vars directory
delegate_to: localhost
run_once: true
file:
path: "host_vars"
state: directory
mode: 0755
# And that each host has it's own directory (but only if we're generating
# a new password for that host).
- name: Create Directory for Stored Generated Values
delegate_to: localhost
file:
path: "host_vars/{{ inventory_hostname }}"
state: directory
mode: 0755
when:
- ansible_password is not defined
- machine_password is not defined
- project_password is not defined
# And lastly, we store the generated password. Ideally, we would use a vault
# at this point, but I don't know how to issue this statement from an ansible
# playbook!
- name: Store Generated Values
delegate_to: localhost
lineinfile:
path: "host_vars/{{ inventory_hostname }}/generated.yml"
regexp: '^machine_password:'
line: 'machine_password: {{ password }}'
state: present
create: yes
when:
- ansible_password is not defined
- machine_password is not defined
- project_password is not defined
# And just because this *is* a test, print it out :)
- name: Print password
delegate_to: localhost
debug: var=password

Following this post, a friend of mine – Jeremy mentioned on Linked In that I should have a look at Ansible Vault. Well, *ideally*, yes, however, when I looked at this code, I couldn’t work out a way of forcing the session to run Vault against a value I’ve just created, short of running something a raw or a shell module like “ansible-vault encrypt {{ file_containing_password }}“. Realistically, if you’re doing a lot with these passwords, you should probably use an external password vault, such as HashiCorp’s Vault or PasswordStore.org’s Pass. Neither of which I tend to use, because it’s just not part of my life yet – but I’ve heard good things about both!

People also assume the same thing about Wi-fi. You reached a log in page, so it must be secure, right? It depends. If you didn’t put in a password to access the Wi-fi in the first place (like in the image of the Windows 10 screen, or on my KDE Desktop) then you’re probably using Unsecured Wi-fi.

An example of a secured Wi-fi sign-in box on Windows 10The same Wi-fi sign in box on KDE Neon

People like to compare network traffic to “sending things through the post”, notablycomparing E-Mail to “sending a postcard”, versus PGP encrypted E-Mail being compared to “sending a sealed letter”. Unencrypted Wi-fi is like using CB. Anyone who can hear your signal can understand what you are saying… but if you visit a website which uses HTTPS, then it’s like listening to someone saying random numbers over the radio.

So, many of these things can be protected against by using a simple method, that many people who provide Wi-fi don’t do.

Turn on WPA2 (the authentication bit). Even if *everyone* uses the same password (which they’d have to for WPA2), the fact you’re logging into the Access Point means it creates a unique shared secret for your session.

“But hang on”, I hear the guy at the back cry, “you used the same password – how does that work?”

OK, so this is where the fun stuff starts. The password is just part of how you negotiate to get on to the network. There’s a complex beast of a method that explains how get a shared unique secret when you’re passing stuff around “in the clear”, and so as a result, when you first connect to that Wi-fi access point, and you hand over your password, it “Authorises” you on to the network, but then hands you over to the encryption part, where you generate a key and then use that to talk to each other. The encryption is the bit like “HTTPS”, where you make it so that people can’t see what you’re looking at.

“I got told that if everyone used the same password” said a hipster in the front row, “I wouldn’t be able to tell them apart.” Aha, not true. You can have a separate passphrase to access the Wi-fi from the Login page, after all, you’ve got to make sure that people aren’t breaking the rules (which they *TOTALLY* read, before clicking “I agree, just get me on the damn Wi-fi already”) by using your network.

Um, no. Well, maybe. See, if they gave you a WPA2 password to log into the Wi-fi, and then the first thing you got to was that login screen, then yep, it’s all good! {*} You can browse with (relative) impunity. But if they didn’t… well, not only are they asking you to shout your secrets on the radio, but if you’re really unlucky, the page asking you to log into Facebook might *also* not actually be Facebook, but another website that just looks like Facebook… after all, I’m sure that page you went to complained that it wasn’t Google or Facebook when you tried to open it…

{*} Except for the fact they’re asking you to tell them not only who you are, but who you’re also friends with, where you went to school, what your hobbies are, what groups you’re in, your date of birth and so on.

But anyway. I understand why those login screens are there. They’re asserting that not only do you understand that you mustn’t use their network for bad things, but that if the police come and ask them who used their network to do something naughty, they can say “He said his name was ‘Bob Smith’ and his email address was ‘bob@example.com’, Officer”…

It also means that the “free” service they provide to you, usually at some great expense (*eye roll*) can get them some return on investment (like, they just got your totally-real-and-not-at-all-made-up-email-address… honest, and they also know what websites you visited while you were there, which they can sell on).

So… What to do the next time you “need” Wi-fi, and there’s a free service there? Always use a VPN when you’re not using a network you trust. If the Wi-fi isn’t using WPA2 encryption (even something as simple as “Buy a drink first” is a great passphrase to use!) point them to this page, and tell them it’s virtually pain free (as long as the passphrase is easy to remember, easy to type and doesn’t have too many weird symbols in) and makes their service more safe and secure for their customers…

One of the things I like to do is to explain how I set things up, but a firewall is one of those things that’s a bit complicated, because it depends on your situation, and what you’re trying to do in your environment. That said, there’s a template that you can probably get away with deploying, and see if it works for your content, and then you’ll see where to add the extra stuff from there. Firewall policies typically work from the top down.

This document will assume you have a simple boundary firewall. This simple firewall has two interfaces, the first being an “Outside” interface, connected to your ISP, with an IPv4 address of 192.0.2.2/24 and a default gateway of 192.0.2.1, it also has a IPv6 address of 2001:db8:123c:abd::2/64 and a default gateway address of 2001:db8:123c:abd::1. The second “Inside” interface, where your protected network is attached, has an IPv4 address of 198.51.100.1/24 and an IPv6 address of 2001:db8:123d:abc::1/64. On this inside interface, the firewall is the default gateway for the inside network.

I’ll be using simple text rules to describe firewall policies, following this format:

So, without further waffling, let’s build a policy. By default all traffic will be logged. In high-traffic environments, you may wish to prevent certain traffic from being logged, but on the whole, I think you shouldn’t really lose firewall logs unless you need to!

Allowing established, related and same-host traffic

This rule is only really needed on iptables based firewalls, as all the commercial vendors (as far as I can tell, at least) already cover this as “standard”. If you’re using UFW (a wrapper to iptables), this rule is covered off already, but essentially it goes a bit like this:

Source Interface: lo (short for "local", where the traffic never leaves the device)
Source IP Address: any
NAT Source IP Address: no
Destination Interface: lo
Destination IP Address: any
NAT Destination IP Address: no
Destination Port: any
Action: allow
Log: no
Notes: This above rule permits traffic between localhost addresses (127.0.0.0/8) or between public addresses on the same host, for example, between two processes without being blocked.

flags: Established OR Related
Action: allow
Log: no
Notes: This above rule is somewhat special, as it looks for specific flags on the packet, that says "If we've already got a session open, let it carry on talking".

Dropping Noisy Traffic

In a network, some proportion of the traffic is going to be “noisy”. Whether it’s broadcast traffic from your application that uses mDNS, or the Windows File Share trying to find like-minded hosts to exchange data… these can fill up your logs, so lets drop the broadcast and multicast IPv4 traffic, and not log them.

Permitting Management Traffic

Typically you want to trust certain machines to access or be accessed by this host – whether it’s your SYSLOG collector, or the box that can manage the firewall policy, so here we’ll create a policy that lets these in.

Allowing Control Traffic

ICMP is a protocol that is fundamental to IPv4 and IPv6. Commonly used for Traceroute and Ping, but also used to perform REJECT responses and that sort of thing. We’re only going to let it be initiated *out* not in. Some people won’t allow this rule, or tailor it to more specific destinations.

Source Interface: inside
Source IP Address: any
NAT Source IP Address: 192.0.2.2 (The firewall IP address which may be replaced with 0.0.0.0 indicating "whatever IP address is bound to the outbound interface")
Destination Interface: outside
Destination IP Address: any
NAT Destination IP Address: no
Destination Port: icmp
Action: allow
Log: yes
Notes: ICMPv4 and ICMPv6 are different things. This is just the ICMPv4 version. IPv4 does require NAT, hence the difference from the IPv6 version below.

Protect the Firewall

There should be no other traffic going to the Firewall, so let’s drop everything. There are two types of “Deny” message – a “Reject” and a “Drop”. A Reject sends a message back from the host which is refusing the connection – usually the end server to say that the service didn’t want to reply to you, but if there’s a box in the middle – like a firewall – this reject (actually an ICMP packet) comes from the firewall instead. In this case it’s identifying that the firewall was refusing the connection for the node, so it advertises the fact the end server is protected by a security box. Instead, firewall administrators tend to use Drop, which just silently discards the initial request, leaving the initiating end to “Time Out”. You’re free to either “Reject” or “Drop” whenever we show “Deny” in the below policies, but bear it in mind that it’s less secure to use Reject than it is to Drop.

Source Interface: any
Source IP Address: any
NAT Source IP Address: no
Destination Interface: any
Destination IP Address: 192.0.2.2, 2001:db8:123c:abd::2, 198.51.100.1 and 2001:db8:123d:abc::1 (may also be represented as :: or 0.0.0.0 depending on the platform)
NAT Destination IP Address: no
Destination Port: any
Action: deny
Log: no
Notes: Drop everything targetted at the firewall IPs. If you have more NICs or additional IP addresses on the firewall, these will also need blocking.

“Normal” Inbound Traffic

After you’ve got your firewall protected, now you can sort out your “normal” traffic flows. I’m going to add a single inbound policy to represent the sort of traffic you might want to configure (in this case a simple web server), but bear in mind some environments don’t have any “inbound” rules (for example, most homes would be in this case), and some might need lots and lots of inbound rules. This is just to give you a flavour on what you might see here.

“Normal” Outbound Traffic

If you’re used to a DSL router, that basically just allows all outbound traffic. We’re going to implement that here. If you want to be more specific about things, you’d define your outbound rules like the inbound rules in the block above… but if you’re not that worried, then this rule below is generally going to be all OK :)

Source Interface: inside
Source IP Address: any
NAT Source IP Address: 192.0.2.2 (The firewall IP address which may be replaced with 0.0.0.0 indicating "whatever IP address is bound to the outbound interface")
Destination Interface: outside
Destination IP Address: any
NAT Destination IP Address: no
Destination Port: any
Action: allow
Log: yes
Notes: This is just the IPv4 version. IPv4 does require NAT, hence the difference from the IPv6 version below.

In my day job, I sometimes need to use a self-signed certificate when building a box. As I love using Ansible, I wanted to make the self-signed certificate piece something that was part of my Ansible workflow.

Here follows a bit of basic code that you could use to work through how the process of creating a self-signed certificate would work. I would strongly recommend using something more production-ready (e.g. LetsEncrypt) when you’re looking to move from “development” to “production” :)

I recently was asked to describe what happens in a penetration test (pentest), how it’s organised and what happens after the test is completed.

Some caveats first:

While I’ve been involved in escorting penetration testers in controlled areas, and helping to provide environments for the tests to occur in, I’ve not been heavily involved in the set-up of one, so some of the details in that area are likely to be a bit fuzzy.

I’m not involved in procurement in any way, so I can’t endorse or discredit any particular testing organisations.

This is a personal viewpoint and doesn’t represent a professional recommendation of how a penetration test should or typically does occur.

So, what actually happens?…

Before the pentest begins, a testing firm would be sourced and the “Terms of Engagement” (TOE), or perhaps a list of requirements would be defined. This might result in a list of tasks that are expected to be performed, and some idea on resources required. It would also be the point where the initiator (the organisation getting the test performed) defines what is “In Scope” (is available to be tested) and what is “Out Of Scope” (and must not be tested).

Some of the usual tasks are:

Internet Scan (the testers will have a testing appliance that will scan all IPs provided to them, and all open ports on those IPs, looking for vulnerable services, servers and responding applications).

Black Box [See note below] Red Team test (the testers are probing the network as though they were malicious outsiders with no knowledge of the system, similar to the sorts of things you might see in hacker movies – go through discovered documentation, socially engineer access to environments, run testing applications like NMAP and Metasploit, and generally see what stuff appears to be publicly accessible, and from there see how the environment appears once you have a foothold).

White Box test (the testers have access to internal documentation and/or source code about the environment they’re testing, and thus can run customised and specific tests against the target environment).

Configuration Analysis (access to servers, source code, firewall policies or network topology documentation intending to check where flaws may have been introduced).

Social Engineering test (see how amenable staff, customers and suppliers are to providing access to the target environment for your testing team).

Some testing firms will also stress test any Denial Of Service Mitigations you may have in-place, but these must be carefully negotiated first with your bandwidth providers, their peering firms and so on, as they will more-than-likely disrupt more than just your services! DO NOT ENGAGE A DOS TEST LIGHTLY!

Once the Terms have been agreed and the duration of these tests have been ironed out (some tests could go on indefinitely, but you wouldn’t *really* want to pay the bills for an indefinite Black Box test, for example!), a project plan is usually defined showing these stages. Depending on the complexity of your environment, I might expect a reasonable duration for a small estate being approximately a day or two for each test. In a larger estate, particularly where little-to-no automation has been implemented, you may find (for example) a thorough Configuration Analysis of your server configurations taking weeks or even months.

Depending on how true-to-life the test “should” be, you may have the Physical Security assessment and Social Engineering tests be considered part of the Black Box test, or perhaps you may purposefully provide some entry point for the testing team to reduce the entry time. Most of the Black Box tests I’ve been involved in supporting have started from giving the testers access to a point inside your trusted network (e.g. a server which has been built for the purpose of giving access to testers or a VPN entry point with a “lax” firewall policy). Others will provide a “standard” asset (e.g. laptop) and user credential to the testing firm. Finally, some environments will put the testing firm through “recruitment” and put them in-situ in the firm for a week or two to bed them in before the testing starts… this is pretty extreme however!!

The Black Box test will typically be run before any others (except perhaps the Social Engineering and Physical Access tests) and without the knowledge of the “normal” administrators. This will also test the responses of the “Blue Team” (the system administrators and any security operations centre teams) to see whether they would notice an in-progress, working attack by a “Red Team” (the attackers).

After the Black Box test is completed, the “Blue Team” may be notified that there was a pentest, and then (providing it is being run) the testing organisation will start a White Box test will be given open access to the tested environment.

The Configuration Check will normally start with hands-on time with members of the “Blue Team” to see configuration and settings, and will compare these settings against known best practices. If there is an application being tested where source code is available to the testers, then they may check the source code against programming bad practices.

Once these tests are performed, the testing organisation will write a report documenting the state of the environment and rate criticality of the flaws against current recommendations.

The report would be submitted to the organisation who requested the test, and then the *real* fun begins – either fixing the flaws, or finger pointing at who let the flaws occur… Oh, and then scheduling the next pentest :)

I hope this has helped people who may be wondering what happens during a pentest!

Just to note – If you want to know more about pentests, and how they work in the real world, check out the podcast “Darknet Diaries“, and in particular episode 6 – “The Beirut Bank Job”. To get an idea of what the pentest is supposed to simulate, (although it’s a fictional series) “Mr Robot” (<- Amazon affiliate link) is very close to how I would imagine a sequence of real-world “Red Team” attacks might look like, and experts seem to agree!

Additional note; 2018-12-12: Following me posting this to the #security channel on the McrTech Slack group, one of the other members of that group (Jay Harris from Digital Interruption) mentioned that I’d conflated a black box test and a red team test. A black box test is like a white box test, but with no documentation or access to the implementing team. It’s much slower than a white box test, because you don’t have access to the people to ask “why did you do this” or “what threat are you trying to mitigate here”. He’s right. This post was based on a previous experience I had with a red team test, but that they’d referred to it as a black box test, because that’s what the engagement started out as. Well spotted Jay!

In this episode, I helped cover the news items, mostly talking about the breach over at NewEgg by the MagePay group and a (now fixed) vulnerability in Alpine Linux, and then did a bit of a dive into IPFS.

It’s a good listen, but the audio right at the end was quite noisy as a storm settled in just as I was recording my outro.

A key message for me, which previously hadn’t been at all clear in IPsec using {free,libre,open}swan is that they refer to Left and Right as being one party and the other… but the node itself works out if it’s “left” or “right” so the *SAME CONFIG* can be used on both machines. GENIUS.

Also, when you’re looking at the config files, anything prefixed with an @ symbol is something that doesn’t need resolving to something else.

It’s well worth a check-out, and it’s inspired me to take another look at IPsec for my personal VPNs :)

I should note that towards the end, Paul tried to run a selection of demonstrations in Opportunistic Encryption (which basically is a way to enable encryption between two nodes, even if you don’t have a pre-established VPN with them). Because of issues with the conference wifi, plus the fact that what he’s demoing isn’t exactly production-grade yet, it doesn’t really work right, and much of the rest of the video (from around 1h10m) is him trying to show that working while attendees are running through the lab, and having conversations about those labs with the attendees.